Synthesis of hyaluronic-acid-related oligosaccharides and analogues, as their 4-methoxyphenyl glycosides, having N-acetyl-β-D-glucosamine at the reducing end

Koen M. Halkes; Ted M. Slaghek; Teija K. Hyppönen; Peter H. Kruiskamp; Tomoya Ogawa; Johannis P. Kamerling; Johannes F.G. Vliegenthart

doi:10.1016/S0008-6215(98)00116-5

Synthesis of hyaluronic-acid-related oligosaccharides and analogues, as their 4-methoxyphenyl glycosides, having N-acetyl-β-D-glucosamine at the reducing end

Koen M. Halkes, Ted M. Slaghek, Teija K. Hyppönen, Peter H. Kruiskamp, Tomoya Ogawa, Johannis P. Kamerling^*, Johannes F.G. Vliegenthart

^*Corresponding author for this work

Wageningen Bioveterinary Research

Research output: Contribution to journal › Article › Academic › peer-review

21 Citations (Scopus)

Abstract

To contribute to the possibilities to study the ability of oligosaccharide fragments of hyaluronic acid to induce angiogenesis, several hyaluronic-acid-related oligosaccharides and their 6-O-sulfated analogues were synthesised as their 4-methoxyphenyl glycosides having 2-acetamido-2-deoxy-D-glucopyranose at the reducing end. In all syntheses described, the D-glucopyranosyluronic acid residue was obtained by oxidation at C-6 of a corresponding D-glucopyranosyl residue after construction of the oligosaccharide backbone, using pyridinium dichromate and acetic anhydride.

Original language	English
Pages (from-to)	161-174
Number of pages	14
Journal	Carbohydrate Research
Volume	309
Issue number	2
DOIs	https://doi.org/10.1016/S0008-6215(98)00116-5
Publication status	Published - May 1998

Keywords

Hyaluronic acid oligosaccharides
Hyaluronic acid sulfated analogues
Oxidation

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Halkes, K. M., Slaghek, T. M., Hyppönen, T. K., Kruiskamp, P. H., Ogawa, T., Kamerling, J. P., & Vliegenthart, J. F. G. (1998). Synthesis of hyaluronic-acid-related oligosaccharides and analogues, as their 4-methoxyphenyl glycosides, having N-acetyl-β-D-glucosamine at the reducing end. Carbohydrate Research, 309(2), 161-174. https://doi.org/10.1016/S0008-6215(98)00116-5

Halkes, Koen M. ; Slaghek, Ted M. ; Hyppönen, Teija K. ; Kruiskamp, Peter H. ; Ogawa, Tomoya ; Kamerling, Johannis P. ; Vliegenthart, Johannes F.G. / Synthesis of hyaluronic-acid-related oligosaccharides and analogues, as their 4-methoxyphenyl glycosides, having N-acetyl-β-D-glucosamine at the reducing end. In: Carbohydrate Research. 1998 ; Vol. 309, No. 2. pp. 161-174.

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abstract = "To contribute to the possibilities to study the ability of oligosaccharide fragments of hyaluronic acid to induce angiogenesis, several hyaluronic-acid-related oligosaccharides and their 6-O-sulfated analogues were synthesised as their 4-methoxyphenyl glycosides having 2-acetamido-2-deoxy-D-glucopyranose at the reducing end. In all syntheses described, the D-glucopyranosyluronic acid residue was obtained by oxidation at C-6 of a corresponding D-glucopyranosyl residue after construction of the oligosaccharide backbone, using pyridinium dichromate and acetic anhydride.",

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Synthesis of hyaluronic-acid-related oligosaccharides and analogues, as their 4-methoxyphenyl glycosides, having N-acetyl-β-D-glucosamine at the reducing end. / Halkes, Koen M.; Slaghek, Ted M.; Hyppönen, Teija K.; Kruiskamp, Peter H.; Ogawa, Tomoya; Kamerling, Johannis P.; Vliegenthart, Johannes F.G.

In: Carbohydrate Research, Vol. 309, No. 2, 05.1998, p. 161-174.

Research output: Contribution to journal › Article › Academic › peer-review

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AU - Hyppönen, Teija K.

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AU - Kamerling, Johannis P.

AU - Vliegenthart, Johannes F.G.

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